diff --git a/src/wp-content/themes/twentynineteen/sass/blocks/_blocks.scss b/src/wp-content/themes/twentynineteen/sass/blocks/_blocks.scss
index 806df3a760..9162cfcd03 100644
--- a/src/wp-content/themes/twentynineteen/sass/blocks/_blocks.scss
+++ b/src/wp-content/themes/twentynineteen/sass/blocks/_blocks.scss
@@ -546,10 +546,13 @@
 		}
 
 		// If an image does not have a left/center/right alignment, 
-		// it's a direct child of .wp-block-img.  If it has no other 
-		// alignment added, we want to make sure the image does not 
-		// extend beyond the width of the text column.
-		&:not(.alignwide):not(.alignfull) > img {
+		// it's a direct child of .wp-block-image.  If it has no other 
+		// alignment added, we want to make sure the image and its 
+		// caption do not extend beyond the width of the text column.
+		&:not(.alignwide):not(.alignfull) > img,
+		&:not(.alignwide):not(.alignfull) > a > img,
+		&:not(.alignwide):not(.alignfull) > img + figcaption,
+		&:not(.alignwide):not(.alignfull) > a + figcaption {
 			@include postContentMaxWidth();
 		}
 
@@ -803,6 +806,8 @@
 		}
 
 		// Ensure images do not expand beyond the column.
+		.wp-block-image:not(.alignwide):not(.alignfull) > img,
+		.wp-block-image:not(.alignwide):not(.alignfull) > a > img,
 		.wp-block-image > img:not(.alignwide):not(.alignfull),
 		.wp-block-image > figure {
 
diff --git a/src/wp-content/themes/twentynineteen/style-rtl.css b/src/wp-content/themes/twentynineteen/style-rtl.css
index 9382635db7..10b62e13b4 100644
--- a/src/wp-content/themes/twentynineteen/style-rtl.css
+++ b/src/wp-content/themes/twentynineteen/style-rtl.css
@@ -5847,13 +5847,19 @@ body.page .main-navigation {
 }
 
 @media only screen and (min-width: 768px) {
-  .entry .entry-content .wp-block-image:not(.alignwide):not(.alignfull) > img {
+  .entry .entry-content .wp-block-image:not(.alignwide):not(.alignfull) > img,
+  .entry .entry-content .wp-block-image:not(.alignwide):not(.alignfull) > a > img,
+  .entry .entry-content .wp-block-image:not(.alignwide):not(.alignfull) > img + figcaption,
+  .entry .entry-content .wp-block-image:not(.alignwide):not(.alignfull) > a + figcaption {
     max-width: calc(8 * (100vw / 12) - 28px);
   }
 }
 
 @media only screen and (min-width: 1168px) {
-  .entry .entry-content .wp-block-image:not(.alignwide):not(.alignfull) > img {
+  .entry .entry-content .wp-block-image:not(.alignwide):not(.alignfull) > img,
+  .entry .entry-content .wp-block-image:not(.alignwide):not(.alignfull) > a > img,
+  .entry .entry-content .wp-block-image:not(.alignwide):not(.alignfull) > img + figcaption,
+  .entry .entry-content .wp-block-image:not(.alignwide):not(.alignfull) > a + figcaption {
     max-width: calc(6 * (100vw / 12) - 28px);
   }
 }
@@ -6181,6 +6187,8 @@ body.page .main-navigation {
 }
 
 @media only screen and (min-width: 768px) {
+  .entry .entry-content .wp-block-columns .wp-block-image:not(.alignwide):not(.alignfull) > img,
+  .entry .entry-content .wp-block-columns .wp-block-image:not(.alignwide):not(.alignfull) > a > img,
   .entry .entry-content .wp-block-columns .wp-block-image > img:not(.alignwide):not(.alignfull),
   .entry .entry-content .wp-block-columns .wp-block-image > figure {
     max-width: 100%;
@@ -6188,6 +6196,8 @@ body.page .main-navigation {
 }
 
 @media only screen and (min-width: 1168px) {
+  .entry .entry-content .wp-block-columns .wp-block-image:not(.alignwide):not(.alignfull) > img,
+  .entry .entry-content .wp-block-columns .wp-block-image:not(.alignwide):not(.alignfull) > a > img,
   .entry .entry-content .wp-block-columns .wp-block-image > img:not(.alignwide):not(.alignfull),
   .entry .entry-content .wp-block-columns .wp-block-image > figure {
     max-width: 100%;
diff --git a/src/wp-content/themes/twentynineteen/style.css b/src/wp-content/themes/twentynineteen/style.css
index dc2ea1ddb8..73a5ce75e7 100644
--- a/src/wp-content/themes/twentynineteen/style.css
+++ b/src/wp-content/themes/twentynineteen/style.css
@@ -5859,13 +5859,19 @@ body.page .main-navigation {
 }
 
 @media only screen and (min-width: 768px) {
-  .entry .entry-content .wp-block-image:not(.alignwide):not(.alignfull) > img {
+  .entry .entry-content .wp-block-image:not(.alignwide):not(.alignfull) > img,
+  .entry .entry-content .wp-block-image:not(.alignwide):not(.alignfull) > a > img,
+  .entry .entry-content .wp-block-image:not(.alignwide):not(.alignfull) > img + figcaption,
+  .entry .entry-content .wp-block-image:not(.alignwide):not(.alignfull) > a + figcaption {
     max-width: calc(8 * (100vw / 12) - 28px);
   }
 }
 
 @media only screen and (min-width: 1168px) {
-  .entry .entry-content .wp-block-image:not(.alignwide):not(.alignfull) > img {
+  .entry .entry-content .wp-block-image:not(.alignwide):not(.alignfull) > img,
+  .entry .entry-content .wp-block-image:not(.alignwide):not(.alignfull) > a > img,
+  .entry .entry-content .wp-block-image:not(.alignwide):not(.alignfull) > img + figcaption,
+  .entry .entry-content .wp-block-image:not(.alignwide):not(.alignfull) > a + figcaption {
     max-width: calc(6 * (100vw / 12) - 28px);
   }
 }
@@ -6193,6 +6199,8 @@ body.page .main-navigation {
 }
 
 @media only screen and (min-width: 768px) {
+  .entry .entry-content .wp-block-columns .wp-block-image:not(.alignwide):not(.alignfull) > img,
+  .entry .entry-content .wp-block-columns .wp-block-image:not(.alignwide):not(.alignfull) > a > img,
   .entry .entry-content .wp-block-columns .wp-block-image > img:not(.alignwide):not(.alignfull),
   .entry .entry-content .wp-block-columns .wp-block-image > figure {
     max-width: 100%;
@@ -6200,6 +6208,8 @@ body.page .main-navigation {
 }
 
 @media only screen and (min-width: 1168px) {
+  .entry .entry-content .wp-block-columns .wp-block-image:not(.alignwide):not(.alignfull) > img,
+  .entry .entry-content .wp-block-columns .wp-block-image:not(.alignwide):not(.alignfull) > a > img,
   .entry .entry-content .wp-block-columns .wp-block-image > img:not(.alignwide):not(.alignfull),
   .entry .entry-content .wp-block-columns .wp-block-image > figure {
     max-width: 100%;